


Three's A Crowd

by abstractSilver (Starlightstiel)



Category: Supernatural
Genre: Anal Fingering, Bottom Dean, Cock & Ball Torture, Cock Rings, Dominant Castiel, Dry Orgasm, F/M, Femdom, M/M, Not Actually Unrequited Love, Orgasm Denial, Painplay, Scratching, Slapping, Threesome - F/M/M, Top Castiel, Voyeurism, references to felching
Language: English
Status: Completed
Published: 2014-02-11
Updated: 2014-02-11
Packaged: 2018-01-11 22:18:04
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,097
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1178616
Author URL: https://archiveofourown.org/users/Starlightstiel/pseuds/abstractSilver
Summary: <blockquote class="userstuff">
              <p>Written for the SPN Kink Meme. Prompt here: http://spnkink-meme.livejournal.com/80640.html?thread=29841664#t29841664 </p><p>She had been toying with him for what felt like hours now, bringing him to the edge of pleasure just to chase it away with sudden pain. It didn't seem that Castiel was going to be an active participant tonight, much to Dean's regret. The angel appeared perfectly content watching the scene play out between the demon and the hunter.</p>
            </blockquote>





	Three's A Crowd

**Author's Note:**

> SUPER graphic, kinky sex. Don't like, don't read. This was written for a prompt over at the Kink meme.  
> Original prompt: http://spnkink-meme.livejournal.com/80640.html?thread=29841664#t29841664
> 
> I needed a break from all of the long wips I have, so I made something porny that actually ended up turning into something pretty depressing.

“What's the matter, Winchester? Afraid of a little demon?” Meg grinned cruelly as she raked her sharp nails down his bare chest. Dean whimpered and jerked back, but the restraints that had been wrapped tightly around his wrists and secured to the headboard kept him from going far. The jagged edges were administered with enough pressure to cause angry red welts to appear on the hunter's chest, just shy of drawing blood. From his position in the dingy chair in the corner of the cheap motel room, Castiel gave the demon a warning growl. 

“Relax Clarence.” Meg rolled her eyes as she reluctantly pulled her hand away from Dean's chest and instead fisted it tightly in his hair, which earned her a moan laced with pleasure and pain. “If he wants me to stop, he knows the magic word.”

Dean didn't answer, just nuzzled his head against her hand in a silent plea for more. She had been toying with him for what felt like hours now, bringing him to the edge of pleasure just to chase it away with sudden pain. It didn't seem that Castiel was going to be an active participant tonight, much to Dean's regret. The angel appeared perfectly content watching the scene play out between the demon and the hunter. 

Meg brought her palm down hard across Dean's already abused cheek, and the human couldn't hold back the cry of pain at the contact. “Pay attention, Dean.” She growled as her fist in his hair tightened even more. “We're just getting started.” 

“Meg, please. Just... Just let me come.” The hunter finally begged, his first words of the night. His abused cock was nearly purple with need, but the tight ring around the base kept relief out of his reach. The demon ran a deceptively gentle finger over the head, and Dean hissed and jerked his hips away. Meg didn't seem to care that her ministrations were only causing pain and discomfort to the oversensitive organ. She continued to run feather-light touches over the head and down the shaft, eventually giving a tight squeeze to his come-heavy balls. 

“What was that? What do you want?” She whispered against the shell of his ear, enjoying the way he was trying in vain to wiggle away from her. Unfortunately for him, she had him by the balls. Quite literally. 

“Come... please.” Dean was such a wreck he couldn't even form coherent sentences anymore, and she knew that even with the ring he wouldn't last much longer. Still, she was going to savor this as long as she could. The mighty Dean Winchester, tied to a bed and begging a demon to let him come. It did wonders for her ego. 

“Not yet princess.” She straddled his thighs and immediately sunk down onto his engorged flesh. He howled in agony as the tight, wet heat enveloped him, and Meg gave him another slap across the face for good measure as she began to ride him. “If you come before I do, I'm going to rip your pretty little dick right off.” 

He just choked back a sob as a tear leaked out of one of his scrunched up eyes. The pain was burning. He was sure that his balls were going to explode if he didn't get some relief soon. There was no pleasure as Meg continued her relentless pace, only pain. He wasn't going to safeword though. No way he was giving that demon bitch the satisfaction. Meg seemed to realize this, if the smug grin she was aiming at him was any indication. She twisted her pelvis on the next down stroke, and it was too much for him. He orgasmed dry with a choked sob, his dick twitching frantically inside of the demon as it tried in vain to spurt something. The ring did its job well though, and if anything the sudden orgasm only made his erection even more painful and desperate. 

“Oh... You're going to regret that.” Meg chided as she slapped him again and then lifted herself off of his still swollen cock. “I was about to let you come, too.”

Dean couldn't take it. He turned his head away from the demon and locked eyes with Castiel, who was still sitting motionlessly in the corner of the room. Castiel would have let him come by now. He never teased him this long. To the point of discomfort, maybe, but never pain. He wondered how far the angel would let this go before he intervened.

The demon seemed to sense what he was thinking, because she immediately grabbed his chin and yanked his head back roughly so he was looking up at her. “Eyes on me now. We want to give angel over there a good show, don't we?” 

Dean moaned pathetically as Meg lowered her mouth to his still-aching cock and licked a wet strip up from the base to the tip. He knew Meg hadn't forgotten her threat; he was dreading finding out what sort of punishment she was going go with this time. Then again, he would almost prefer a good whipping to the gentle suckling she was currently applying to his oversensitive cock. She continued to bob her head up and down as her devious fingers worked their way slowly around his ass and parted the flesh there. He tensed up as her dry digits traced his hole. He hadn't been penetrated yet tonight, and if she stuck something up there without lube, even something as small as a finger, it was going to hurt like hell. 

“What's the matter little baby, going to cry?” She teased as she roughly jammed one finger into his entrance, causing him to seize up and cry out with sudden pain. 

“F-fuck you.” He managed to spit out as she slowly rotated her finger inside of him. The dry burn was agonizingly painful, but his futile attempt at closing his legs to the intrusion was met with a derisive laugh and another finger being jammed inside next to the first. 

Dean felt a gush of blood rush into his mouth as he bit down hard on his lip to keep from screaming. Meg seemed almost impressed that he managed to keep quiet if her expression was anything to go by. She leaned over him and bit one of his nipples hard enough to bruise while her fingers continued their dry stretching. He wasn't going to be able to walk straight for a week, and it wouldn't be in the good way. 

Meg once again lowered her mouth onto his cock, and he silently prepared himself for more torturous teasing. That definitely isn't what he got. Without any warning at all, the demon bit down _hard_ on his shaft. 

Dean was in so much pain he couldn't even breathe. His vision clouded as he began to thrash against the bonds. He was vaguely aware of the ties holding his wrists falling away and someone's hands caressing his face as he writhed on the bed. It wasn't until he saw concerned blue that his heart began to calm slightly and he realized that he had been crying out the angel's name. 

Castiel looked pissed, and he was relieved that the angel's ire wasn't directed at him. Meg was standing several feet from the bed and she looked both irritated and frightened. She must have known she had gone too far. Castiel continued to glare at her as he gathered Dean up into his arms and began to stroke the hunter's hair comfortingly. Dean would never admit it out loud, but he almost enjoyed it when the angel babied him like this after an especially rough session. 

Meg held up her hands defensively from where she stood. “He didn't safeword.” 

“You hurt him.” Castiel spat, his words filled with venom. Dean was once again glad he wasn't on the receiving end. He knew firsthand how scary the angel could be when he was pissed. 

“Oh come on.” Meg rolled her eyes. “You do way worse than that to me on a regular basis.” 

“You can handle it. He's human.” 

Dean was a bit offended that Castiel was talking about him like he was some weakling that needed to be played nicely with, but it was worth it for the thunderous expression on Meg's face. He knew that the way Castiel treated him irked the demon. That just made Dean like it even more. He nuzzled closer against Castiel and delighted in the way that the angel rubbed soothing circles on his back. Dean normally hated sappy stuff like this, but after a session with Meg it was pretty much a necessity. 

“Cas?” Dean finally managed to say when he felt like he was calm enough to speak somewhat normally. The angel tore his scathing glare away from Meg and looked at the hunter with fondness and concern. 

“Are you alright Dean?”

“Um...” He looked down at his painful erection and Castiel nodded in understanding. The angel gently removed the cock ring and Dean felt like crying in relief as Castiel wrapped a hand around his shaft and slowly stroked up and down.

It took hardly any time at all for Dean to finally come. He spilled over Castiel’s hand and onto the bedding beneath them. When he finally finished (he had a lot to get out), he collapsed, boneless, in the angel’s arms and forced himself to take deep breaths. He distantly heard Meg and Castiel arguing over something, but he was so exhausted he couldn’t really make out what it was and at this point he didn’t really care. 

He grumbled sleepily as he felt someone shaking him gently, and eventually opened an eye to glare accusingly at Castiel. The angel smiled apologetically. “You can’t sleep yet, Dean.” 

“Why?” He whined, nuzzling his head back against Castiel’s chest and closing his eyes. 

“You know why.” Castiel whispered softly against his forehead as he pressed a tender kiss there. Dean sighed and forced himself to sit up despite the protests from his aching body. Meg was now sitting on the bed as well, a scowl on her face, and Dean glared at her as he leaned into Castiel’s soothing touch.

“Meg.” Castiel prompted. The demon groaned and rolled her eyes. 

“Fine. I’m sorry for biting your pathetic and, if I might add, tiny cock.” 

Castiel gave her a warning growl, and she countered with a scathing glare. “Okay, okay. Fine. I’m sorry for breaking the terms of our agreement by inflicting you with cruelty and excessive pain… pansy.” 

Castiel sighed but didn’t complain, obviously realizing that was as close to a real apology the demon would ever agree to give. Dean just leaned against Castiel’s shoulder and tried to force his eyes to stay open. The angel placed soft kisses against Dean’s cheek and shoulders, and Dean couldn’t help but grin at the absolutely hateful look Meg was giving him in response to Castiel’s affections. Dean had never seen him treat her with any tenderness at all. 

Castiel was seriously weird about aftercare, and he refused to let Dean sleep or go anywhere until he had practically killed him with affection, especially after a hard session like tonight had been. It was kinda weird. Outside of the bedroom, Castiel was anything but kind and gentle with him. More often than not, the angel was yelling at him and calling him an idiot for various reasons, the most common scenario being when he and Sam were about ready to be monster chow and he had to pray to Castiel for a quick rescue. No, his loving tenderness must have just been another kink, like how the angel loved to suck his own come out of Dean’s ass after he had fucked him senseless, or how he enjoyed watching while Meg dominated the hell out of him. 

He knew Castiel would never feel the same way that Dean did. For Castiel, this was about sex and probably power. Dean knew that for himself, it was something more. As he slowly drifted off to sleep, Castiel’s wide blue eyes full of love as he lay beside him on the bed and held him close, he let himself pretend that maybe Castiel really did feel something more for him. He tried to push that hope somewhere deep inside though, so he wouldn’t have to face the inevitable disappointment it would bring. He felt Castiel shift beside him and pull his body close, still laying tender kisses against his flesh. Yes, it was so easy to pretend.

**Author's Note:**

> I hope you enjoyed it! That is probably the most kink sex scene I've written to date lol. Let me know if you enjoyed it! :3


End file.
